methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate | 934281-62-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate
• 英文别名: Methyl 1-(2-acetyloxyethoxymethyl)-5-bromo-1,2,4-triazole-3-carboxylate
• CAS: 934281-62-6
• 化学式: C₉H₁₂BrN₃O₅
• 分子量: 322.115
• InChiKey: NSXOPBWMGUTOTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate 在 四(三苯基膦)钯 氨 、 lithium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 48.25h， 生成 5-(2-furanyl)-1-[(2-hydroxyethoxy)methyl]-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution

  摘要：

  5-Aryltriazole acyclonucleosides with various aromatic groups on the triazole ring were synthesized via the Suzuki coupling reaction in aqueous solution and promoted by microwave irradiation. Careful optimization of the reaction conditions led in good to excellent yields to the Suzuki products, while the cyclization side-reaction could be completely suppressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.154
• 作为产物：
  描述：

  阿昔洛韦侧链 、 5-溴-1,2,4-三唑-3-甲酸甲酯 在 对甲苯磺酸 作用下， 反应 0.5h， 以28%的产率得到methyl 1-((2-acetoxyethoxy)methyl)-5-bromo-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Direct synthesis of 5-aryltriazole acyclonucleosides via Suzuki coupling in aqueous solution

  摘要：

  5-Aryltriazole acyclonucleosides with various aromatic groups on the triazole ring were synthesized via the Suzuki coupling reaction in aqueous solution and promoted by microwave irradiation. Careful optimization of the reaction conditions led in good to excellent yields to the Suzuki products, while the cyclization side-reaction could be completely suppressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.154

文献信息

• Synthesis and Binding Properties of a New Fluorescent Molecular Sensor Based on a Triazole Nucleoside
  作者：Lijuan Guo、De-Hua Zhang、Duanyi-Ping、Ze-Shan Xiong、Yan Liu

  DOI：10.3184/174751916x14737808687253

  日期：2016.10

  A new fluorescent nucleoside based on 1,2,4-triazole nucleoside has been synthesised and its X-ray structure determined. Its binding properties, investigated by fluorescence spectroscopy, show that it can selectively bind Hg2+ with fluorescence quenching.

  合成了一种基于 1,2,4-三唑核苷的新型荧光核苷，并确定了其 X 射线结构。通过荧光光谱研究其结合特性表明它可以选择性地结合 Hg2+ 并具有荧光猝灭作用。
• An Efficient Mixed-Ligand Pd Catalytic System to Promote CN Coupling for the Synthesis of N-Arylaminotriazole Nucleosides
  作者：Yuting Fan、Yi Xia、Jingjie Tang、Fabio Ziarelli、Fanqi Qu、Palma Rocchi、Juan L. Iovanna、Ling Peng

  DOI：10.1002/chem.201103918

  日期：2012.2.20

  Make it unique! A mixed‐ligand system of Pd/Synphos/Xantphos promotes effective CN coupling in the synthesis of various N‐arylaminotriazole and N‐arylaminopurine nucleoside analogues. This catalytic system is strikingly powerful and efficient, allowing for unparalleled substrate scope and high product yields as well as promotion of CCl bond activation for CN coupling (see scheme).

  使其独一无二！的Pd / Synphos /加入Xantphos的混合配体系统促进有效的C  N的各个的合成耦合Ñ -arylaminotriazole和Ñ -arylaminopurine核苷类似物。该催化体系是惊人地有力和有效的，从而允许无与伦比的底物范围和高的产物收率以及促进的C 对于C Cl键活化 N个耦合（参见方案）。
• Microwave promoted C–O coupling for synthesizing O-aryloxytriazole nucleoside analogues
  作者：Mei Cong、Yi Xia、Jingjie Tang、Laurence Borge、Gilles Quéléver、Juan L. Iovanna、Palma Rocchi、Ling Peng

  DOI：10.1039/c4nj02284j

  日期：——

  A convenient and effective microwave-promoted synthesis of O-aryloxytriazole nucleosides was established, leading to an interesting candidate with anticancer activity.

  建立了一种方便有效的微波促进合成O-芳氧基三唑核苷类化合物的方法，得到一种具有抗癌活性的有趣候选化合物。
• Fluorescent Chemosensor for Pb2+ Based on 1,2,4-Triazole
  作者：D.-H. Zhang、Y.-P. Duan、Y. Liu

  DOI：10.1134/s0022476618050220

  日期：2018.9

  A new fluorescent sensor for Pb2+ based on functionalized 1,2,4-triazole is synthesized. The crystal structure and molecular conformation is confirmed by single crystal X-ray diffraction. Its binding properties investigated by fluorescence spectroscopy show that it can selectively bind Pb2+ with fluorescence quenching.

  合成了一种基于功能化 1,2,4-三唑的新型 Pb2+ 荧光传感器。晶体结构和分子构象由单晶 X 射线衍射证实。通过荧光光谱研究其结合特性表明它可以通过荧光猝灭选择性地结合 Pb2+。
• S-Aryltriazole acyclonucleosides: Synthesis and biological evaluation against hepatitis C virus
  作者：Yang Liu、Yi Xia、Wei Li、Mei Cong、Alain Maggiani、Pieter Leyssen、Fanqi Qu、Johan Neyts、Ling Peng

  DOI：10.1016/j.bmcl.2010.04.115

  日期：2010.6

  Novel S-aryltriazole acyclonucleosides were designed as structural analogs based on the previously identified antiviral aryltriazole acyclonucleosides in our laboratories. These S-aryltriazole nucleosides were synthesized in excellent yields via SNAr-mediated S-arylation, followed by subsequent ammonolysis. X-ray structural analysis revealed special structural feature brought by the S-linkage, which may represent an unfavorable factor contributing to the lack of anti-HCV activity for this family of triazole nucleosides. (C) 2010 Elsevier Ltd. All rights reserved.